Tryhackme Cct2019 ~upd~ May 2026

room on TryHackMe, originally from the US Navy Cyber Competition Team, is less of a linear story and more of a gritty, disconnected puzzle set. However, when you piece the forensic and reversing challenges together, a narrative of

espionage, digital smuggling, and high-stakes cinematic references The "Put Together" Story

The narrative arc of CCT2019 feels like a modern techno-thriller where you play an investigator tracking a cell of sophisticated hackers: The Digital Handshake

: The story begins with a suspicious traffic capture. An unknown group has been passing sensitive files over an unconventional port—specifically The Cinematic Cipher

: You discover the files aren't just encrypted; they are wrapped in

. In a nod to 90s hacker culture, the "password" protecting this digital contraband is BER5348833

—the same identification used by Angela Bennett in the classic film The Hidden Payload

: Once you break the encryption, the story moves into the "RE" (Reverse Engineering) phase. You are no longer just looking at traffic; you are dissecting the custom tools the hackers left behind to understand their next move. Room Context : Created by the US Navy Cyber Competition Team and sponsored by the US TENTH Fleet Difficulty : Rated as

, reflecting the high-level forensic skills required to "put together" the clues. Core Skills : You will need to master PCAP analysis Cryptcat decryption Assembly-level reversing to finish the tale. or a guide to the RE3 reversing challenge? CCT2019 - TryHackMe

TryHackMe CCT2019: A Comprehensive Guide to the Challenge

TryHackMe is a popular online platform that offers a variety of virtual hacking challenges and tutorials for individuals looking to improve their cybersecurity skills. One of the most notable challenges on the platform is the CCT2019 challenge, which is designed to simulate a real-world hacking scenario. In this article, we will provide a comprehensive guide to the TryHackMe CCT2019 challenge, including a walkthrough of the challenge, tips and tricks, and a discussion of the skills and knowledge required to complete it.

What is the TryHackMe CCT2019 Challenge?

The CCT2019 challenge on TryHackMe is a virtual hacking challenge that is designed to test a participant's skills in penetration testing, vulnerability assessment, and exploitation. The challenge is based on a real-world scenario and involves hacking into a virtual machine (VM) to gain access to sensitive information. The challenge is designed for intermediate-level hackers and is intended to provide a realistic simulation of a penetration testing engagement.

Objective of the Challenge

The objective of the CCT2019 challenge is to gain access to the VM and retrieve a sensitive file that contains critical information. The challenge involves several stages, including:

1. Reconnaissance: Gathering information about the target VM and identifying potential vulnerabilities.
2. Exploitation: Exploiting vulnerabilities to gain access to the VM.
3. Post-exploitation: Navigating the VM and retrieving the sensitive file.

Walkthrough of the Challenge

To complete the CCT2019 challenge, participants must follow a series of steps that involve reconnaissance, exploitation, and post-exploitation. Here is a walkthrough of the challenge:

Step 1: Reconnaissance

The first step in the challenge is to gather information about the target VM. This can be done using tools such as Nmap, which is a popular network scanning tool. Participants must scan the VM to identify open ports and services.

nmap -sV <IP address of VM>

The scan results will reveal open ports and services, including a web server running on port 80.

Step 2: Identifying Vulnerabilities

Once the open ports and services have been identified, participants must look for potential vulnerabilities. In this case, the web server is running a vulnerable version of Apache. Participants can use tools such as Nikto to scan the web server for vulnerabilities.

nikto -h <IP address of VM>

The Nikto scan will reveal a potential vulnerability in the Apache version.

Step 3: Exploitation

With the vulnerability identified, participants can use a tool such as Metasploit to exploit the vulnerability and gain access to the VM. tryhackme cct2019

msfconsole
use exploit/apache/mod_cgid_oob
set RHOST <IP address of VM>
set LHOST <IP address of your machine>
exploit

The exploit will provide a shell on the VM.

Step 4: Post-exploitation

Once participants have gained access to the VM, they must navigate the file system to retrieve the sensitive file. This involves using basic Linux commands such as cd, ls, and cat to navigate the file system.

cd /home/user
ls
cat sensitive_file.txt

The sensitive file will contain critical information that is required to complete the challenge.

Tips and Tricks

Here are some tips and tricks that can help participants complete the CCT2019 challenge:

• Use the right tools for the job: Make sure to use the right tools for each stage of the challenge. For example, use Nmap for reconnaissance and Metasploit for exploitation.
• Read the challenge description carefully: The challenge description will provide important information about the target VM and the objective of the challenge.
• Work methodically: Take your time and work methodically through each stage of the challenge.

Skills and Knowledge Required

To complete the CCT2019 challenge, participants will need to have a good understanding of the following skills and knowledge:

• Penetration testing methodologies: Participants should have a good understanding of penetration testing methodologies, including reconnaissance, exploitation, and post-exploitation.
• Vulnerability assessment: Participants should be able to identify potential vulnerabilities in a target system.
• Exploitation: Participants should be able to exploit vulnerabilities to gain access to a target system.
• Linux command-line interface: Participants should be familiar with the Linux command-line interface and be able to navigate a Linux file system.

Conclusion

The TryHackMe CCT2019 challenge is a comprehensive and realistic simulation of a penetration testing engagement. By completing the challenge, participants can gain valuable experience and skills in penetration testing, vulnerability assessment, and exploitation. With the right tools and knowledge, participants can successfully complete the challenge and improve their cybersecurity skills.

Phase 2: Web Enumeration (Gobuster & Manual Browsing)

The website is a simple "under construction" or default page. This is a trick. You need to find hidden directories.

Tool: Gobuster or Dirb.

gobuster dir -u http://<target_ip> -w /usr/share/wordlists/dirb/common.txt

Findings: You should discover a notable directory, such as /admin or /console. For CCT2019, the gold is a console or dashboard page that allows command execution.

Context and Origin

CCT2019 was released as part of TryHackMe’s early effort to host realistic team-based cyber challenges. It mirrors the format of the UK Cyber Security Council’s Cyber Challenge events, where competitors face a simulated corporate network with multiple services, users, and vulnerabilities. The year “2019” denotes the original challenge edition.

Unlike typical CTFs with standalone flags, CCT2019 presents a progressive attack chain:

• External web application foothold
• Lateral movement to an internal host
• Privilege escalation on two separate machines
• Capturing final flags that require chaining multiple exploits

Phase 2: Privilege Escalation on Machine 1

• LinPEAS or manual enumeration shows:
  • sudo -l: user can run /usr/bin/python as root without password.
  • Python privilege escalation (sudo python -c 'import pty;pty.spawn("/bin/bash")') yields root on Machine 1.
• First flag located in /root/flag1.txt.

6. Conclusion

The TryHackMe CCT2019 room is an excellent introductory CTF that reinforces essential penetration testing steps:

1. Enumerate thoroughly – hidden directories and source code comments are goldmines.
2. Crack hashes – weak algorithms like MD5 are still prevalent.
3. Reuse discovered credentials – across services (MySQL password ≠ SSH, but hints lead to valid creds).
4. Escalate via cron – always check scheduled tasks when you have write access.

This room is highly recommended for beginners progressing from basic Linux commands to realistic privilege escalation techniques.

The CCT2019 room on TryHackMe is a high-difficulty "Insane" rated room featuring legacy challenges from the U.S. Navy Cyber Competition Team 2019 Assessment. It is widely reviewed as a deep, multi-layered puzzle that prioritizes analytical reasoning and evidence-based validation over the fast-paced "grab-the-flag" style typical of many Capture The Flag (CTF) events. Key Skills & Challenges

The room is built as a structured assessment rather than a standard machine exploitation lab. It forces you to question every artifact and avoid assumptions.

Deep Traffic Analysis: You will face complex PCAP analysis tasks. Reviewers note that these often include intentional red herrings and misleading paths to test your ability to stay focused on relevant data.

Reverse Engineering (RE): Challenges involve analyzing binaries to understand their execution logic. You cannot simply extract strings; you must use tools like dnSpy to decompile and debug .NET applications.

Forensics & Payload Recovery: A significant portion involves reconstructing traffic and recovering payloads from raw captures.

Cryptographic Puzzles: The room uses layered cryptography where each step is dependent on correctly interpreting the previous one. Specific ciphers mentioned by users include the Rail Fence cipher.

Zero Trust Mindset: The room is designed to simulate real-world investigations where nothing is assumed valid until proven by evidence. Community Perspectives room on TryHackMe, originally from the US Navy

Users who have completed the room highlight its unique "puzzle" feel and the importance of accuracy in early steps to avoid being locked out of later stages.

“This wasn't a fast-paced CTF or a “grab-the-flag” room. It felt more like a structured assessment, designed to test how well you can analyze, verify, and reason under pressure.” LinkedIn · Harshit Gupta · 3 months ago

“It is very important to do the first step correctly. If you don't recover the first file in its entirety, you may not be able to complete steps later on in the challenge.” GitHub

These walkthroughs and reviews offer a deep dive into the specific tasks and the 'Insane' difficulty level of the CCT2019 challenges: TryHackMe #702 CCT2019 (Insane) 902 views · 2 years ago YouTube · Adamski CTF TryHackMe - CCT2019 (part 2) 1K views · 4 years ago YouTube · Dysnome [ASMR] TryHackMe - CCT2019 (part 1) 3K views · 4 years ago YouTube · Dysnome CCT2019 - TryHackMe

The CCT2019 room on TryHackMe is a collection of legacy challenges originally designed for the U.S. Navy Cyber Competition Team (CCT) 2019 Assessment. Unlike standard "boot-to-root" machines, this room focuses on analytical depth, packet analysis, and reverse engineering, requiring users to verify every piece of evidence rather than just rushing for a flag. The room is divided into several specialized tasks: Task 1: CCT2019 - pcap1 (Packet Analysis) Task 2: CCT2019 - re3 (Reverse Engineering) Task 3: CCT2019 - for1 (Forensics) Task 4: CCT2019 - crypto1 (Cryptography) Task 1: PCAP Analysis (pcap1)

This challenge tests your ability to reconstruct data from raw network traffic. The primary goal is to analyze a packet capture file and extract relevant files or credentials.

Key Focus: Use Wireshark to inspect the traffic. Look specifically for file transfers (HTTP/FTP) or encrypted communications that can be decrypted.

Crucial Step: You must recover the first file in its entirety. If the initial file recovery is incomplete, subsequent steps in the challenge may become impossible to solve.

Avoid Rabbit Holes: The creator warns that this is strictly a PCAP challenge. If you find yourself performing steganography or advanced reverse engineering in this specific task, you are likely off track. Task 2: Reverse Engineering (re3)

The re3 task involves analyzing a compiled binary to understand its internal logic. In this challenge, you aren't just looking for static strings; you must understand the execution flow.

Tools to Use: For .NET applications, tools like dnSpy are recommended for decompiling and viewing the source code. Walkthrough of the Challenge To complete the CCT2019

The Logic: One walkthrough of this task highlights a requirement to find factors of a specific number (e.g., 711,000,000) and test combinations to find the correct key for a set of "sliders" within the application. Task 3 & 4: Forensics and Cryptography

These tasks round out the assessment by testing your ability to handle digital artifacts and broken encryption.

Forensics (for1): Requires deep diving into file headers and metadata.

Cryptography (crypto1): Often involves layered encryption where each step depends on the correct interpretation of the previous artifact. Strategy for Success To complete the CCT2019 room, adopt a Zero Trust mindset:

Question Everything: Artifacts may contain "red herrings" designed to lead you down rabbit holes.

Validate Evidence: Ensure every step is backed by evidence found within the provided files.

Use the Right Tools: Have a toolkit ready that includes Wireshark, dnSpy, and standard Linux forensics tools. TryHackMe, London, UK TryHackMe_and_HackTheBox/CCT2019.md at master - GitHub

Introduction

TryHackMe is an online platform that provides a virtual environment for penetration testing and cybersecurity training. The CCT2019 challenge is one of the many virtual machines (VMs) available on the platform, designed to simulate a real-world cybersecurity scenario. In this essay, we will walk through the steps to compromise the CCT2019 VM and highlight the key learning points from the challenge.

Initial Reconnaissance

Upon launching the CCT2019 VM on TryHackMe, the first step is to perform an initial reconnaissance of the target system. This involves scanning the VM's IP address to identify open ports and services. Using the nmap command, we scan the VM's IP address: nmap -sV <IP address>. The scan reveals several open ports, including FTP (20), SSH (22), and HTTP (80).

Identifying Vulnerabilities

The next step is to identify potential vulnerabilities on the target system. We notice that the FTP service is running on port 20, and a quick search on the internet reveals that the version of FTP running on the VM is vulnerable to a buffer overflow attack. Additionally, the HTTP service on port 80 appears to be running a web application that may be vulnerable to SQL injection.

Exploiting Vulnerabilities

Using the information gathered during the reconnaissance phase, we proceed to exploit the identified vulnerabilities. We use the vsftpd exploit to gain access to the FTP service and create a new user account. With the new user account, we can log in to the system via SSH.

Alternatively, we can also use the SQL injection vulnerability on the web application to inject malicious SQL code and extract sensitive data, such as user credentials.

Post-Exploitation

Once we gain access to the system, we perform a thorough enumeration of the system to identify sensitive data and configuration files. We discover a configuration file that contains a hidden directory, which leads to a backup file containing a hashed password.

Using a password cracking tool, such as John the Ripper, we crack the hashed password and gain access to the root account.

Conclusion

The TryHackMe CCT2019 challenge provides a realistic simulation of a cybersecurity scenario, allowing us to practice our penetration testing skills in a safe and controlled environment. Throughout the challenge, we performed initial reconnaissance, identified vulnerabilities, exploited them, and conducted post-exploitation activities to gain access to sensitive data.

The key learning points from this challenge include:

1. Scanning and enumeration: The importance of thorough scanning and enumeration to identify open ports, services, and potential vulnerabilities.
2. Vulnerability identification: The need to research and identify potential vulnerabilities on the target system.
3. Exploitation: The use of exploits to gain access to the system and create a foothold for further exploitation.
4. Post-exploitation: The importance of thorough enumeration and configuration file analysis to identify sensitive data and escalate privileges.

By completing the CCT2019 challenge on TryHackMe, we have gained valuable experience in penetration testing and vulnerability exploitation, which can be applied to real-world cybersecurity scenarios.